Search Cheap Flights to
Windsor

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windsor Flights as Low as $492

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 5 hours ago
$492
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $492 found 5 hours ago
JetBlue Airways
Sat, Sep 19 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 5 hours ago
$502
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Sep 19 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $502 found 5 hours ago
JetBlue Airways
Wed, Sep 16 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 3 hours ago
$503
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $503 found 3 hours ago
United
Fri, Sep 25 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$508 Roundtrip, found 5 hours ago
$508
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $508 found 5 hours ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 2 days ago
$511
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $511 found 2 days ago
JetBlue Airways
Sat, Sep 19 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 5 hours ago
$512
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Sep 19 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $512 found 5 hours ago
JetBlue Airways
Wed, Sep 16 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 3 hours ago
$513
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $513 found 3 hours ago
United
Fri, Sep 25 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 2 days ago
$513
Roundtrip
found 2 days ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $513 found 2 days ago
JetBlue Airways
Wed, Sep 16 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 3 hours ago
$514
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $514 found 3 hours ago
United
Mon, Sep 14 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$519 Roundtrip, just found
$519
Roundtrip
just found
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $519 just found
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$521 Roundtrip, found 2 days ago
$521
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $521 found 2 days ago
Delta
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$522 Roundtrip, found 2 days ago
$522
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $522 found 2 days ago
United
Mon, Sep 14 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, just found
$524
Roundtrip
just found
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $524 just found
JetBlue Airways
Wed, Sep 16 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 3 hours ago
$524
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $524 found 3 hours ago
JetBlue Airways
Tue, Sep 15 - Sat, Oct 3
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$528 Roundtrip, found 2 days ago
$528
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 15 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Oct 3, priced at $528 found 2 days ago
United
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$578 Roundtrip, found 5 days ago
$578
Roundtrip
found 5 days ago
Select United flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $578 found 5 days ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $492, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $492 right now, why wait?

Windsor Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$491

Last Minute Hotel Deals in Windsor

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Get rates
Align Inn Vermont
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in ...
8.4/10 Very Good! (1,005 reviews)
"There is some renovation, but nothing to inconvenience you. Beautiful Inn, nice dining area, pool, hot tub and exeercise facility. Very friendly staff. Great continental breakfast included. Close proximity to everything."

Reviewed on Jun 25, 2026

Get rates
Fireside Inn & Suites West Lebanon
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.4/10 Good! (1,001 reviews)
"We loved the large beautiful hot tub outside and the firepit. We spent a lot of time there. Staff was amazing food was good."

Reviewed on Jun 23, 2026

Get rates
Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (589 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

Get rates
Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,002 reviews)
"Beautiful "on-mountain" property. Rooms were clean. Plenty of food at breakfast with tons of complimentary water bottles to stay hydrated. JP made our group's stay memorable with his warm hospitality."

Reviewed on Jun 28, 2026

Get rates
The Mountain Inn at Killington
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,002 reviews)
"I always find my stays at Holiday Inns to be enjoyable. Staff was very nice. Breakfast was good. Room was large and comfortable. Conveniently located."

Reviewed on Jun 26, 2026

Get rates
Holiday Inn Express Hotel & Suites White River Junction by IHG
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,001 reviews)
"This is a beautiful hotel with friendly hlpful employees. My only complaint was that the breakfast food was not hot. They need new food warmers. Otherwise a great place."

Reviewed on Jun 28, 2026

Get rates
On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (952 reviews)
"The room was very large and had a lovely view of the grounds and river. And having a grocery store across the street was a plus. I do have two suggestions. First, the room was not well lit. As I said, the room was quite spacious, but only had two small lamps so it was quite dim. There were many electrical ..."

Reviewed on Jun 29, 2026

Get rates
The Shire Woodstock
See all 2,654 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.